As a beginner last year, the hardest part was choosing the telescope because you just don't know what's out there unless you do some serious research. When i have friends over and i ask "want to look a the moon or a planet with my telescope?" they are shocked when i bring out the R2D2 looking dob because a telescope in their mind must be a refractor looking telescope. They always say "when you said telescope i thought you meant a
telescope!" LOL Anyway after explaining how the truss dob works and after looking into the eyepiece they appreciate the dob.
When i was looking to purchase last year, GO-TO dobs were only just coming out and were more expensive than they are now. If i were to be in the same predicament this year i would have gone with a smaller 8" go-to rather than my 10" manual dob simply for the tracking ability. I don't regret buying the 10" dob as i've learned more about the sky than i could have imagined however after buying it i found out about things like collimation, eyepieces, mirror cooling & dew... what a nightmare! However, i have found that i hardly ever need to collimate even though i collapse the scope after every session ( i havn't collimated at all this year). Mirror cooling hasn't affected me too much as i leave the scope under the carport or back deck if i plan to go out but dew has affected me a few times.
As as for eyepieces, i was amazed with what the standard ones provided but i have recently purchased my first premium - a Pentax XW 10mm and i plan to get a Televue 24mm panoptic soon. Wideviews make it much easier with manual scopes! Though i'm open to suggestions
The problem with a lot of beginners is that they think they can spend $100-$200 on a complete setup and get great views. Beginners have so many choices these days but i agree that you really need to spend about $500 minimum when buying new to get something that isn't going to disappoint and make you lose interest.
And about the whole collimation thing, telling a beginner that they need to collimate everytime they use the scope will just scare them away from dobs. I don't think you need to collimate modern dobs regularly hardly at all! At least not mine
cheers